Between Then and Now
by lollipopbirdie
Summary: Castiel Novak, an aspiring writer and traveler, has finally settled into his new home in Chicago, content with leaving everyone from his past behind. But Dean Winchester unexpectedly stumbles back into his life, only to be whisked away just as quickly. Fortunately, fate isn't finished with them yet. A Supernatural AU.
1. Chapter 1

**January 22**

The jingling of bells above a heavy glass door welcomed Castiel Novak into Brews Brothers on a crisp, Friday morning. He inhaled the thick aroma of coffee grounds and vanilla bean, savoring the warmth that soothed his wind bitten cheeks. Over the past few months, the small shop on the corner of 76th street had become a regular stop for him in the mornings. But he still hadn't gotten tired of the atmosphere. The limited space had proved cozy instead of cramped, the dim lighting and close-seated tables giving it a homey feel. He closed the gap between him and the counter quickly, anxious for his morning cup, and was met by a young, sprightly barista.

"You're three minutes late this morning, Mr. Novak," the boy remarked playfully. Castiel glanced at the clock above the menu. 8:48.

"Good morning to you too, Damien," he replied, chuckling lightly.

"Large cappuccino, t-"

"Two shots espresso, one shot vanilla, and an oat and honey scone." Castiel raised an eyebrow as the barista finished his sentence and slid his pre-made order out from behind the counter. "Oh, don't look so surprised. You've come here every morning for the past five months." He laughed and shook his head, pulling out a few bills and holding them out.

"It's on the house," Damien said, a slight flush creeping across his pale cheeks. Castiel eyed him, taking a sip from his drink. The boy was the definition of cute, dark brown hair casually mussed up and large, pale blue eyes that took up just enough of his slender face, but that's exactly what he was. A _boy. _He couldn't be any older than nineteen.

"You're too much," he smirked, stuffing the bills into a tip jar and walking away before Damien could object. As he maneuvered towards his seat in the far corner of the shop, he knew that the barista was looking after him. Setting down his order at the small table for one, he unlatched his bag and pulled out his laptop, a parting gift from his brother Gabriel, and flipped it open, sliding into his seat. After a few clicks, his email was opened. **Unread-22. **Castiel grimaced. Work was the last thing he wanted to do, but, hey, it was Friday. It'd be over soon.

A half a cup of coffee, three-fourths of a honey scone, and nine emails later, the bells over the door jingled again. Castiel looked up from his work. There weren't usually many people in the coffee shop this time in the morning, especially not in the cold of January, and he knew all the regulars. His attention piqued as a young man stepped through the door, dark leather jacket turned up against the harsh, Chicago wind. Attractive male was _not _usually on the menu. He watched as the man stepped up to the counter, not bothering to turn down the collar of his coat.

"Large black coffee, please." His low, rough voice traveled through the room.

"Name?" The man glanced around slightly, probably noting the lack of customers waiting for their order. Castiel had noticed that for the first few weeks, too. No matter how few people were waiting for their coffee, Damien always insisted on asking the purchaser's name. The only time he didn't was when Castiel walked through the doors.

"Uh, Dean," the man responded quizzically. Damien scrawled on the cup quickly.

"Coming right up." As the customer turned to walk to the pickup section of the counter, Castiel caught a glimpse of his face. And, God _damn_, was he attractive. The collar of his jacket framed soft, sculpted cheekbones that were flushed with cold and sprinkled with freckles. Soft, pink lips curled into a small smirk, and light brown hair that stuck up wildly off his forehead. But, oh, his _eyes. _Green apple irises sparkled like gems under dark, wispy lashes and Castiel was immediately transfixed. Dean turned away after a moment, unaware of the onlooker, and he tried to return to his work. But it was hard. One quick glance confirmed Castiel's speculations. He had an amazing ass.

Taking a deep breath, he flicked his eyes back to his computer, attempting to keep his interest at bay. Leering at people while they're waiting for coffee was something he definitely knew not to do.

_Dean, _he repeated to himself in his mind. Suddenly, something clicked. The green eyes, the splay of freckles… Memories of a little boy in an over-sized leather jacket insisting he took half of his peanut butter sandwich in the Lincoln Elementary cafeteria flooded his mind. _Dean Winchester. _

Hesitantly, he shut his laptop, weighing the options. He should probably leave the man alone to enjoy his coffee, never running the risk of looking like an idiot if Dean didn't remember him. That was the safe option. On the other hand, he could walk over and sit down with an extremely attractive male from his past who had once defended him on the first grade playground. He sighed lightly and pushed his chair back, legs letting out a screech that echoed through the shop. Striding over to the small table where the man now sat, pushed up against the brick wall of the shop, he took a deep breath.

"Dean Winchester?" The man looked up, startled, and his green eyes nearly took Castiel's breath away. As the startled glance slowly melted into a frown, he realized he was staring. "Oh, uh, I'm Castiel Novak." He watched for any kind of recognition in his eyes, but got none.

_Who is this guy? _Dean thought to himself, slightly annoyed. He wasn't too bothered by the interruption, since the guy wasn't too hard on the eyes. _He's fucking gorgeous, _something whispered in the back of his mind, and he shook it off quickly. But no matter how attractive he was, the man's staring was making him a little uncomfortable.

"We, um, we were in Miss Mills first grade class together at Lincoln Elementary, I think." Castiel hesitated. "You punched a kid who pushed me off the playground and we ate lunch together for a few days after that." Dean's frown quickly turned into a more relaxed expression when he started to remember.

"You're the kid who wouldn't take off his mangled trench coat." Castiel bowed slightly, comically.

"In the flesh." The man's deep laugh tickled his ears and made him blush slightly. "May I?" Castiel motioned to the chair on the other side of the table.

"'Course!" He nodded and sat down quickly. "Well, man, how you been? I always wondered what happened to you."

"My parents moved us up to Omaha, actually."

"Hm." Dean crossed his arms and leaned back in his chair. "And then what?" Castiel raised his eyebrow and tilted his head.

"What do you mean?" The man across from him grinned crookedly.

"I mean what'd ya do after that? Figure the best way to catch up is to ask what happened between then and now. "

"Oh! Well high school, I guess, then I got an English degree at a community college, got a job, then-"

"What kind of job?" Castiel glanced up to see Dean peering down at him, genuinely interested.

"It's-It's kind of hard to explain…"

"Try." The twinkle in his eyes seemed to dare him to go in to detail.

"At first, I was a receptionist at a publishing company in Denver, and then one of the editors got a hold of some of my writing and liked it. Quite a bit actually. I started writing articles for their paper and it kind of expanded from there. Now I, well, I write travel books."

"You're kidding?" He interrupted, smirking.

"No, I'm not, actually," Castiel continued, shooting him a look. "I know it sounds boring, but I've always loved traveling. And writing, for that matter. The job lets me do both."

"So, a traveler, huh?" Dean gave him a once over and he suddenly became self-conscious of the rumpled t-shirt he'd thrown on under an old windbreaker he'd pulled out of the back of his closet. "I could see that." Instead of asking what that meant, he continued.

"This is going to sound cheesy, but I love seeing the things that God has created." Dean's eyebrow shot up.

"You pretty religious?" Castiel shook his head, laughing.

"No, not really. My family is, though, and that's really the only thing that stuck." He nodded, pleased with the answer.

"So is Chicago one of your 'exotic destinations'?" he asked, teasingly.

"I don't do exotic. Just national. And to answer your question, no, it's not. I moved here a couple of months ago, and I'm between jobs right now." He paused, checking for Dean's interest. It was definitely there.

"Why are you so interested in this?" he asked, sitting back in his chair and smiling slightly. "No one ever is." Dean leaned forward onto his elbows, smirking.

"You're pretty god damn interesting, Cas." Castiel's breath caught as another memory tickled the back of his mind.

"You called me Cas," he commented quietly. "You did that before, too." Dean fell back and smiled warmly.

"I guess I did." They held each other's gaze a few moments longer than necessary before Castiel broke away, clearing his throat.

"Well, anyways, I'm working on my own thing now. A book actually."

"About?"

"Uh, well, places around the country that aren't well-known and should be."

"America's secrets?" Castiel grinned.

"I guess you could call them that."

"Well, I'll be sure to pick myself up a copy. When's is comin' out?"

"Oh gosh, not for another few years at least. There's tons of research to be done," he gestured to his laptop a few tables away, "and then the travelling and finally writing it and getting it published."

"That sounds like a shit load 'a work."

"Yeah, it's a lot, but I am very excited." He smiled at the man across from him. "But enough about me. What did you do after Lincoln?" Dean's smile seemed to falter as the conversation was turned towards him.

"High school till junior year, then worked as a mechanic at my Uncle Bobby's shop and was a bus boy on the side."

"May I ask why?" Dean's eyes flick up to meet Castiel's. "I'm sorry, I know that's personal…"

"No, it's fine. My dad died when I was 16 and I dropped out to help my mom pay the bills an' put my little brother through school."

"Oh…" He glanced away, wishing he hadn't asked. "I'm sorry."

"Nah, it's fine. The only thing that son of a bitch was good for was teachin' me how to fix a car when he was anywhere near sober." Dean laughed lightly and Cas did too, just to fit the mood. "Anyway, I lived in Lawrence till a few months ago. Came here, got settled, landed a job, the works."

"Where do you work?"

"Now? A record store down on 67th street, but I wanna go into law enforcement someday."

"Police?" Dean shook his head, taking a drink of his coffee.

"Firefighter."

"So you're into risking your life for others?" Dean smirked at his question.

"I just like the idea of saving people, ya know? Getting away from the family business."

"Is that why you moved here? To get away from it?"

"Kinda. My brother, Sammy, is a lawyer-in-training at Stanford and flew the coop a while ago. I felt like it was my turn." Castiel nodded at him in understanding.

"Do you have any other siblings?"

"Nah, just me an' Sam. What about you?" Taking a breath, Castiel tried to keep his face composed. His family wasn't anywhere near a comfortable subject for him, but he didn't want to make that know.

"Six," he replied, as cheerfully as possible.

"Six?" Dean's eyebrows shot up in disbelief and Castiel nods. "Holy crap, those must be some interesting family dinners." Castiel almost flinched at his comment.

"Yeah…" Dean gazed down at the man, understanding his hesitation. It was obvious he's uncomfortable with the topic.

"We don't have to talk about them if you don't want. I know what it feels like to have some family issues." Castiel nodded and glanced up at him apologetically.

"Actually…" Dean eyed the clock over the counter. 9:35. "Shit," he mumbled. He looked back across the table to see the man watching him, confused.

"I'm really sorry but I gotta go. I was s'possed to be at work five minutes ago." Castiel's heart sunk.

"Oh, that's fine!" Dean smiled at him and got up, coffee in hand, reluctantly walking towards the door. After a few steps, he turned back around.

"Cas, do…" The words to ask him out were on the tip of his tongue, but he held them back. "Do you come here every day?" He nodded.

"Only on weekdays, though. Do you?" he asked, knowing fully well he didn't. Dean's eyes lit up and he smirked.

"I do now." Castiel repressed a grin as a flush crept across his cheeks.

"I'll see you Monday then?" Dean's smile grew wider.

"See ya Monday." When the jingling of bells told the shop that Dean Winchester had left the building, Castiel let the smile take over his face. What a morning! Getting up, he walked back to his table, quickly finishing his order and packing up his laptop. He zipped his coat up as far as it would go and stepped back out into the cold, not wanting to wait a whole weekend for Monday to come.

* * *

On Monday morning, at 8:45 on the dot, Castiel was back at the Brews Brothers counter.

"The usual?"

"Yeah, and a large black coffee." Damien raised an eyebrow at him questioningly, but Castiel didn't see. He was too busy glancing around anxiously, bouncing lightly on the balls of his feet. He slid a few bills across the counter and took his order, shooting a half-hearted smile to the barista, and walked to the table where he and Dean had sat the other day. Flipping open his laptop, he clicked on a few things, scrolling through pages, but his mind was elsewhere. He couldn't help but to smile when he thought about the way Dean had taken such an interest in him. Besides Gabriel, no one else had really ever cared. Castiel sipped his coffee quietly, stomach too twisted to take in much, and watched the clock, looking over his shoulder every time the bell on the door jingled.

By 10:00, he had given up. Spirits crushed, he tossed the remnants of his order and the untouched black coffee into the trash.

_Maybe he just forgot, _he told himself, walking out of the building. _People get busy. It happens. _But those thoughts didn't make him feel any better.

By the following Friday, Dean still hadn't shown, and Castiel had stopped glancing at the door every time it opened. And after a few weeks, the meeting was at the

back of his mind.

* * *

**A/N: I hope the first chapter was as intriguing as I wanted it to be! I am super excited about this fic. There's only going to be a few chapters, and those will be uploaded about once a week, hopefully more. And please review! This is my first AU story and I'd love to hear your guy's feedback! **


	2. Chapter 2

**Note: Wow, okay, so this chapter turned out to be a lot longer and harder to write than anticipated... Hope it's enjoyable!**

* * *

**October 22- 1 year and 9 months later**

_Who the hell invites the dropout to a high school reunion? _Dean Winchester wondered cynically as padded slowly into his dim-lit bedroom, grabbing his buzzing cellphone off the dresser and flipping it open.

"Yep?"

"Hey, Dean." His brother voice crackled though the other line.

"Heya, Sammy, what's up?" Walking over to the cracked mirror in the corner of the room, he held the phone to his ear and started buttoning up the white dress shirt that hung loosely on his damp skin. The fabric clung as he tugged at it, fumbling the buttons with one hand while holding the phone with the other.

"You going to Ellen and Bobby's for dinner tomorrow night?" _Shit. _

"Yeah, yeah, 'course, wouldn't miss it."

"You forgot about it, didn't you?" He sighed, knowing Sam was right.

"Sorry, man, just got a lot on my mind this week. But I'll be there, 'kay?"

"A lot on your mind?" He took the ignorance of his answer as a yes.

"Yeah, I have this friggin' high school reunion tonight an' I've been tryin' to figure out how to get out of it."

"They invited a dropout to the ten-year reunion?" Sam asked quizzically.

"Exactly!" Tucking in the rest of his shirt into the only pair of black pants he owned, Dean fidgeted, trying to get the fabric to lie comfortably. Dress clothes had never been his thing.

"Why are you even going? I mean, I know high school wasn't that great. D'ya really want to give up a 'precious' night home alone to relive it?"

"Hell, no. But... Charlie made me." His brother's light laughed sounded in his ear as he turned to his bed.

"Good for her. What time's it at, anyway?"

"Eight," he mumbled, mulling over his small collection of ties.

"Dude, that's, like, right now."

"Yeah, yeah, I know," he replied, flicking some water out of his hair absent-mindedly. In the late afternoon, Dean had "accidentally" fallen asleep on his couch in hopes that'd he'd sleep right through the event. Unfortunately, he'd woken up sweaty, in desperate need of a shower, and with just enough time left to be hopelessly late.

"Will ya ask Jess what tie I should wear?" Muffled voices on the other end of the phone call answered his request. His brother's longtime girlfriend, Jessica, had helped him out with situations like this ever since she moved back to Kansas with Sam.

"She says she needs to know what else you're wearing."

"Black pants, white shirt." Another pause.

"She says you're boring, and I have to agree." Dean pursed his lips, trying to wrestle his foot into a shoe while standing.

"Tell her I don't give a rat's ass." His brother laughed loudly and relayed the message to Jess and, after a moment, he heard her voice in the background.

"She says black tie, or red if you're feeling adventurous."

"Black it is," he smirked, just to spite them. Sam chuckled lightly as he grabbed the strip of fabric and slung it around his neck.

"So we'll see you tomorrow?"

"Yep."

"Great. Tell Charlie hey from me."

"Will do," he muttered, attempting to tie his tie while holding the receiver to his ear with a shoulder.

"See ya, Dean." The line went dead and he flipped the phone closed, pocketing it and folding down his collar. The mirror in front of his was dusty and cracked, but he could see enough of himself to feel ridiculous.

_I look like a god damn FBI agent, _he thought, making a face at the reflection and rolling up his sleeves. That was about as good as it was going to get, because one quick glance at the clock told him that he should have left at least 20 minutes ago. Charlie was going to bite his head off if he ran much later.

Hitting the light switch, he took one last glance at the room he lived in. The small heaps of clothing only added to the lackluster of the stained walls and faded carpeting in it. Besides the small twin bed shoved up in the corner of the room, a small wooden dresser and his old guitar were the only other objects in it. The rest of his possessions had been boxed up and left sitting in his Uncle's basement. He promised himself that he'd move into a better place as soon as he got the money, but had said that since the day he moved in. Even so, the apartment had grown on him. Grabbing the keys to his Impala off the make-shift dining room table, he sped out the door and down the steps, counting the minutes till he could return home.

* * *

After a twenty-minute car ride, Dean pulled into the parking lot of Edlund High School, a place he had never expected to return to. Its stout brick walls looked exactly the same as they had all those years ago, which didn't make him any more excited to be there. Gravel crunched beneath his feet as he made his way towards the door, a warm October wind rustling the trees around the building. Joining the small stream of latecomers outside of the front entrance, he ran his hands through his windblown hair, hoping it'd dried enough during the drive. He found a place at the back of the line and scanned the small crowd around him. Not a single face was familiar, but he hadn't expected them to be. Besides a few of his closest friends and maybe a girl or two that he dated, he didn't really remember anyone from the class. But that wasn't a bad thing. The school wasn't a high point in his life, that was for sure, and the less he remembered about it, the better. Stepping through the doors, the first thing he saw was a blur of red, before being enveloped in a bony hug.

"You came! I knew you would!" He laughed softly, squeezing the girl in his arms.

"Nice to see you too, Charlie."

* * *

Forty five minutes later, Dean stood alone in the cafeteria, arms crossed, searching the crowd for the overly excited redhead. Charlie had dragged him into the thick of things within minutes of arriving, only to abandon him at the first sight of one of her old friends. He'd survived making painful small talk with a handful of people before removing himself from the action, thoroughly put out.

Tugging on the collar of his white shirt, he felt a bead of sweat trail down his temple. The host had moved the reunion to the cafeteria last-minute, and the new room was barely half the size of the previous setting. It was completely packed, the unusually humid air adding to the stickiness of the atmosphere. Colored streamers hung half-heartedly off the beige walls and a few plastic-covered tables were scattered throughout the crowd. The main focus was the DJ table crammed in to the far corner of the room, shinning obnoxiously bright lights around the dim setting. Dean loosened his tie and began to shove his way through the crowd to find Charlie. He had to get out of there. Maybe he could plead sick, or say that he had to work early the next morning. She would definitely see through any excuse he came up with, but it was worth a shot. In the thick of the crowd, he heard a voice call out beside him.

"Dean! Over here!" Turning slowly, he saw Charlie a few feet away, waving him over. Sighing, he reluctantly made his way towards her, knowing she had an old classmate for him to talk to. As soon as he was within reach, she grabbed his arm, pulling him the rest of the way.

"You remember Garth, right?" she asked, nodding towards the scrawny little guy in front of them. _No. _

"Yeah, totally!" he replied, plastering a fake grin on his face.

"So this is the infamous Dean Winchester," the man said in a high-pitched voice that matched his figure.

"Infamous?" he repeated, raising an eyebrow. Garth smirked.

"You know, bad-boy drop out who always pulled the prettiest girls into the first floor janitor's closet?"

"Oh… yeah," Dean replied, laughing with the two, uneasy that stranger knew about him.

As soon as Charlie started jabbering on, he tuned out, scanning the room. The entrance was only ten, maybe fifteen feet in front of him. If he could get away from the conversation for a few seconds, he would be a free man. Dean was about to return his attention to Charlie when something caught his eye. A man stepped through the front doors, clearly alone and uncomfortable. His icy blue eyes flicked from face to face in the crowd, searching for somewhere to be. After a moment, they landed on Dean, and his heart sped up. Even after almost two years, he still would've recognized that face anywhere. Dean only looked away for a moment, mumbling his excuses to Charlie, before making his way through towards the door. The man watched him the entire time, head tilted slightly in confusion.

Dean couldn't help the grin that took over his face as he worked his way towards the entrance. Although he would never admit it, he'd missed the guy. A lot. It made no sense, seeing that they'd only talked for an hour since first grade, but there was just something different about him. In Dean's opinion, it felt like they had known each other for much longer. After a few feet of pushing and shoving, he broke through the edge of the crowd, situating himself in front of the man he'd been dying to see for almost two years.

"Heya, Cas." Castiel Novak stood in front of him, brow still furrowed in bewilderment. To Dean, he looked almost exactly the same as he had the cold day in Brew Brothers, but had traded his t-shirt and windbreaker for a black, fitted suit, and bright blue tie. His strong, square jaw was covered lightly with stubble, surrounding thick, pink lips that were turned down slightly. Tousled, brown hair still stuck up randomly, giving him a younger appearance, and his crystal blue eyes still shone brighter than anything Dean had ever seen.

"Dean Winchester?" His stomach fluttered at the sound of the man's rough, gravelly voice. Remembering their previous conversation, Dean bowed slightly, mocking what Castiel had done.

"In the flesh." But his excitement was curbed when he noticed that his enthusiasm wasn't being returned. "You do remember me, right?" Castiel blinked a few times, snapping out of whatever trance he had sunk into at the sight of him.

"Yes, of course, but… Why are you here?" Dean laughed lightly.

"It's a high school reunion. Why do you think?"

"You went here?"

"Yeah, 'course!" But then he realized what the man was thinking. How could they have never noticed that they went to school together? "I dropped out in the beginning junior year, remember?"

"Oh…" Confusion slowly drained from Castiel's face. "I started here in the middle of it."

"Well, then, that explains it! How've you been, man?" He asked, clapping him on the shoulder. The man's arm was stiff under his grasp.

"I've, uh, been fine." Castiel's awkwardness baffled him. He'd been so open, so comfortable the last time they talked, but now…

"You okay?"

"Yeah, yeah it's just that…" Castiel paused, averting his eyes, "it's been a while since we last talked and you, well, you didn't-"

"I didn't show up that Monday." The man swallowed hard, still not meeting his eyes, and nodded. A pang of guilt flashed through Dean's chest as he realized that Castiel thought he had skipped out.

"Look, this is gonna sound stupid, but I had a family thing." Castiel cast his gaze up, unsure. He'd been ditched plenty of times before, and that line wasn't new to him.

"No, really, I did! It's not just some lousy excuse, I swear. If I had skipped out, I'd have come up with a much better story than that." Still uneasy about the situation, he nodded mutely and glanced away, flashing only a hint of a smile. Dean sighed loudly and leaned closer to him, catching his eye once again.

"Cas, I really wish I coulda been there. You gotta believe me." His sincere gaze faded into a smirk. "And, I haffta say, that coffee was pretty damn good. I woulda come back just for that." Castiel found himself grinning, even though he wasn't sure he believed him. Dean's smirk had haunted his dreams for the past few months, and having the real thing wasn't something he could resist. Seeing that Castiel had noticeably cheered up, Dean repeated his question.

"So, really, how've ya been?"

"I've been well, and you?" Dean's smile grew wider.

"Pretty damn good now that-"

"Dean!" Startled by the screech that rang out behind him, Dean spun around, only to be enveloped in the arms of a very attractive brunette. Castiel watched as the two embraced and, after a moment, started talking. But the way the woman batted her eyes and leaned into Dean sparked a jealousy in him that was hard to keep down. He knew it was completely illogical to have feelings for the man, but he couldn't help it. For reasons unbeknownst to him, Dean had made a lasting impression. A few minutes later, the conversation ended with another hug that lasted a moment too long, and Dean turned back to him. But to his surprised and relief, he looked more exasperated than he did pleased.

"Who was that?"

"Some girl I dated a while back." Castiel's stomach dropped. "Natalie's her name, I think."

"Oh, that's… nice." Dean smirked at the hesitation in his voice.

"What about you?" Castiel eyed the man questioningly.

"What do you mean?"

"I mean who'd you d-"

"_Ladies and gentlemen, it's time to get this party started!"_ Dean grimaced as the DJ's voice erupted from the speakers. Within seconds, music started blaring and cheers rang out from the crowd. He rolled his eyes and let out a deep sigh. Glancing at the man beside him, he saw that Castiel looked just about as pleased with the noise as he did.

"You wanna get out of here?" he asked, struggling to hear his own voice over the roar. Castiel nodded quickly, relieved at the excuse to leave the room. He followed Dean out of the doors and into the silent, empty hallways of the school. It took mere seconds for the music to fade completely behind them and when it did, Dean continued.

"What I was tryin' to ask before that son of a bitch interrupted was if you dated anyone in high school." Castiel hesitated, following the man down the empty hallway, not knowing how he'd react to his answer.

"Meg Masters." Dean stopped in his tracks, eyeing him quizzically.

"Short? Dark brown hair? That Meg?" Castiel nodded. "Huh…"

"What?"

"She just doesn't seem like your type."

"And what do you think my type is?" he asked mockingly, continuing down the hallway.

"Oh, I dunno," Dean replied, smiling slightly, picking up his pace to match Castiel's. "She just seemed pretty cut-throat. Intense." He laughed.

"That she was. And you're right about her not being my type, but that was for other reasons."

Dean cast a glance at the man next to him, wanting to ask him what those reasons were, but kept quiet. He was pretty sure he already knew.

"What about now? You with anyone?" Castiel smirked and turned to him.

"Dean, is that _flirtation_?"

If the person asking the question had been anyone else, Dean would have had a smooth and snappy comeback on the tip of his tongue. But the way the man's eyes were glinting teasingly, already knowing the answer, made him stumble. Why did the guy have to be so god damn attractive? A flush crept across his cheeks as he glanced away, clearing his throat.

"If it were, not saying that it is, but _if_…" He paused, peering at the man beside him, "what, uh, what would you think?" Castiel laughed softly, his smirk spreading into a grin.

"_If _it were, I don't think I would mind." Dean exhaled, completely relieved, and held the other man's gaze for a moment longer than necessary as they walked slowly down the hallway.

"So, uh, how's your…" Out of the corner of his eye, Dean noticed what seemed to be double doors leading to the gym, and trailed off. Backtracking, he read the sign that had been posted on it.** UNDER CONSTRUCTION-NO ENTRY. **He shoved the door open anyways.

"Uh, Dean? It says 'no entry'." He turned to Castiel, shrugging and holding the door open for him. The man squinted at him before letting his shoulder fall forward in defeat. "But I take it you're not one for rules," Castiel mumbled as he stepped reluctantly through the doorway. Chuckling, Dean followed close behind.

The room they had entered was huge, lit only by a few dim, buzzing lights overhead. Bleachers stretched on either side of what once was a gym floor. Now, it seemed that all the tiles had been torn up, exposing a large, gray slab of concrete. The panels had been piled in the far corner of the gym, near a group of bulky construction equipment. Dean raced ahead of Castiel, who was still hesitant about being in the room at all, and pounded up the bleachers near them.

"Be quiet!" he hissed as soon as the noise had stopped echoing. "Someone could hear!"

"So?" Dean called back, standing on the topmost bleacher and spreading his arms wide. "Come on, Cas, have a little fun!" Castiel huffed and started climbing, making as little noise as possible. Dean grinned at his annoyance and met him halfway, sliding into one of the seats.

"So, Cas, what've you been up to? Between then and now?" Castiel sat next to him, a little closer than Dean would normally been comfortable with, but he didn't mind so much.

"Quite a bit, actually."

"Like what?" He glanced over at Dean, who was gazing at him like he was the most interesting thing in the world, and his heart fluttered. The feeling of someone actually caring about what he had to say was something Castiel hadn't felt since the last time they talked, and he had forgotten how great it was.

"Remember the book that I talked about before?" Dean nodded. "Well, that got picked up much faster than expected and I started travelling. I've made stops all around the country for about six months now."

"That's great!" Castiel blushed at the man's obvious enthusiasm for his work.

"It has been very enjoyable. But what about you? I assume you moved back here at one point." Dean's smile faltered and he turned away, scanning scene in front of them. "Yeah, I did. My mom passed away about two years ago. That was the family thing I was talkin' about earlier."

"Oh, I'm… I'm very sorry…" Castiel trailed off, not sure how to continue.

"S'okay ." Dean took a deep breath and leaned back against the bleachers. "But, anyway, I moved back here about a week after that. Just felt like I should be closer to home, ya know? Then I got my ol' job back at my Uncle Bobby's repair shop and moved to a crappy apartment on the other side of town. It's been pretty much the same since."

"Well, that sounds-"

"Boring?" Dean interrupted. Castiel smiled at him sympathetically. "It kinda is. Ain't near as exciting as travelling around the country." His grin grew wider and Dean laughed lightly, cheering up a bit. "What are you doing here anyways? After all you've been doin', you decide to stop in at a high school you went to for a year and a half?" Castiel just shrugged.

"I was in the area. I didn't think it would hurt to stop by. High school wasn't too fun for me, but there are a few people I would like to catch up with."

"What was wrong with it? High school, I mean."

"Oh, well… My people skills have always been rusty, at best. That caused a few problems." Castiel laughed lightly to himself, reflecting on some of his worst days. "I was shy and quite awkward, and people never hesitated to point that out."

"I wish I coulda been there," Dean replied, nudging the man gently with his arm. "Woulda put those son's 'a bitches in their place, if ya know what I mean." Castiel smiled his comment, wondering for a moment what it would have been like if Dean was there.

"What about you? You don't seem like one to frequent events like this."

"Hell, no, but my friend Charlie wanted me to. And she doesn't take no for an answer. You'd like her. I'll introduce you two later, if you want."

"I'd like that." Dean glanced up to see Castiel grinning at him and he smiled back. The evening wasn't turning out to be nearly as bad as he expected.

"I'm pretty glad I came, though." Castiel tilted his head to the side in a confused state, and Dean could only guess if he was teasing him or not.

"Why is that?" Licking his lips, Dean swept his eyes over the man for a quick second, before letting a smirk return to his face.

"'Cause 'a you, man." Castiel's face flushed red at his words and he looks down at his feet, cheeks bunching up as he tried and failed to suppress a grin. Dean watched the man for a moment, smiling himself, before clearing his throat. "Look, Cas, I know this is a little forward but-"

"_What the hell are you two doing?!"_ Their heads snapped up simultaneously, both spotting the stocky security guard filling the doorway on the other side of the gym.

"Oh, _shit!" _Dean rose in an instant, pulling Castiel with him. "Come on, Cas!" He flew down the bleachers after him without taking a moment to stop and think.

"_Hey!" _The security guard's heavy footsteps echoed through the room but neither of them looked back. Dean shoved open the door to the gym and Castiel slipped through, following him a ways down the hallway, only stopping when he did.

"You think we lost 'em?" Dean asked, smirking and breathing hard. He was answered by the sound of doors slamming and heavy footsteps tracing the path they just took.

"_Come back 'ere!" _

"God dammit…" Dean sprinted down the rest of the hallway and turned the sharp corner, leaving Castiel to follow blindly. But when he rounded the wall, Dean had disappeared. He slowed his pace as he looked around, bewildered. The hallway was completely and utterly deserted.

"Dean?" All of a sudden, he was yanked roughly by the arm and enveloped into darkness. Dazed, he spun around, acutely aware of a figure near him. But his eyes quickly adjusted to the lack of light. Dean was standing inches in front of him, eyes glinting and playful, and he could see a bit of light around a door behind them. He could tell the room was cramped and small, and he assumed it was some sort of supply closet.

"Dean, what are-" His mouth was covered by a hand before he could finish his sentence and the man hushed him as he slid an arm around his waist, holding him still. Dean tensed up when he heard footsteps right outside the door, padding slowly around the hallway. They passed after a moment and he relaxed, but didn't let go of Castiel. The man's breath on his hand and the warmth of his body beneath his suit made his heart beat skyrocket. Swallowing hard, he peered down in to Castiel's eyes, which were gazing up at him expectantly.

He knew he shouldn't try anything. That would involve putting himself out there without knowing if the feelings are requited, which was a risk Dean was rarely willing to take. But his head was clouded with the intoxication of having Castiel so close to him, silencing the warning bells. Before he could talk himself out of it, Dean removed his hand, leaning down and gently covering Castiel's lips with his own. Every nerve in his body erupted into sparks at the touch and he pressed further, relishing the man's soft mouth beneath his. Dean pulled away after a moment, breathless, blinking his eyes open slowly. And to his relief, Castiel was beaming at him.

"Was that okay?" he asked sheepishly. Castiel smirked mischievously, pulling gently on Dean's tie.

"Don't ask stupid questions," he murmured, stepping backwards, dragging Dean with him. With one arm wrapped around Castiel's waist and the other hand laced through his hair, Dean kissed him again, roughly, stubble scratching across his chin. Castiel buzzed beneath his touch, letting himself be pinned up against the bare wall. His hands flitted nervously over Dean's back before settling on his hips. Pulling away for a moment, Dean kissed the side of Castiel's face, trailing his lips down his jaw. His skin burned red-hot wherever the man's mouth touched. Dean pressed up against him, fitting their bodies together, and slid his suit jacket off his shoulder, yanking at the collar of his shirt. Castiel's grasp tightened on his hips as Dean nipped the soft skin at the base of his throat.

"Dean…" he muttered, so faintly that he wasn't sure if he said it aloud. Dean's smile against his collar bone assured him that he had.

"Mm hm?" But he didn't have time to respond before Dean's mouth was covering his again, tongue gently sliding between his parted lips. His breath caught in his throat as he felt his shirt being untucked roughly, his stomach jumping as Dean's hands ran over his torso. Castiel savored the sensation, kissing the man back fiercely. His hands roamed over Dean's back and shoulders, itching to flip him around and take control. But he stayed put, grasp settling on the back of his neck, easing him closer and deepening the kiss.

It was only when Dean's hands started working their way up, taking his shirt with them, that a bit of reality sunk in. If things went any further, they'd be in that closet all night. Castiel pulled away as much as he could, which wasn't very much at all, and tried to put a bit of force into his voice.

"Dean, I-" But the man's hands were persistent, his lips even more so, and he was silenced quickly. The buttons of his shirt popped open as Dean's fingers roamed up his sides, sending chills through his body. Castiel tilted his head away reluctantly, and Dean's lips quickly shifted to his neck. The threat of forgetting what he had to say loomed overhead.

"Please, we can't…" At his words, Dean froze. He took a step back and quickly removed his hands, anxiety clawing at his insides.

"No, no, that's not what I meant," Castiel continued hastily, realizing what he had said. Dean exhaled deeply, relief flooding him. "W-we can, we definitely can." Flustered, Castiel blushed, stumbling over his words. "Just not here. Not now. I-I need to go talk to… talk to people and t-then later…" His mind scattered as Dean smirked at him, obviously amused by his nervous rambling.

"Cas, I get it. No need to freak out." After a moment of silence, he turned and swung open the door, letting in the harsh light. A grin spread slowly across his face when he saw Castiel, completely disheveled. His white shirt was untucked and halfway buttoned, the collar sitting crookedly on his neck, his blue tie hung loosely, partially undone, and his dark brown hair stuck up wildly after being mussed and combed through by Dean's fingers. The red flush on his cheeks grew even brighter as Dean stared, and he hurriedly buttoned his shirt, averting his eyes. Dean bent down and grabbed the suit jacket, which was crumpled on the floor, and handed it to him. Castiel took it without a word or even a glance up. His self-consciousness was clear.

Seeing that he'd made the man uncomfortable, Dean let his shoulder sag and his gaze fall. The familiar feelings of guilt and regret took ahold of him.

"Look, Cas, I'm sorry if that was too much or, uh, not what you wanted, or somethin' like that."

"No, Dean, it's not… I just haven't been… been kissed like that in a long time," Castiel explained sheepishly, casting an apologetic look at the man in front of him as ran a hand through his hair to flatten it. "I liked it quite a bit."

"Yeah, me too," he replied, overwhelmed with relief. "Well, more than a bit but…" This time, it was Dean who blushed. Castiel smiled at him, feeling more at ease than he had a moment ago.

"Do I look alright?" he asked, spreading his arms slightly and shrugging. "Back to normal, I mean." Dean sucked in a sharp breath as he cast a glance over the man. "Normal" was a huge understatement

Swallowing hard, he nodded softly, a smile playing at his lips as he tried to calm a part of him that was _very _happy to see Castiel standing there. But when he noticed his tie, which was still askew, he stepped over, straightening it for him and smoothing down his collar. A grin spread involuntarily across his face as Castiel's bright blue eyes gazed up into his innocently, almost childlike.

"I get you later tonight, right?" he muttered before he even realized what he was saying.

At his words, an icy hand grasped Castiel's throat, making him choke back the answer that had almost come so easily. Reality crashed down on him, crushing any hopes that had bloomed in his mind. How could he have let himself forget?

_No, you don't, _he thought as an answer. But instead of saying that aloud, he only nodded, forcing his face into a tight smile. But the hesitance went unnoticed by Dean, whose perception was clouded by how perfect the situation seemed. As they walked out of the room and through the halls, Dean's arm slung around Castiel's shoulder, it never once crossed his mind that everything was too good to be true.

* * *

Two hours later, Castiel excused himself from his last conversation of the night. He made his way through the crowd, which had barely thinned, to the back of the room. Glancing at the clock, he grimaced. His flight was scheduled to leave in less than 7 hours. Castiel took a breath and scanned the setting, eyes searching for Dean. Throughout the evening, he had considered leaving without saying goodbye. It seemed like the safer and easier option. But he knew that he couldn't do that to Dean, or to himself.

Finally, he spotted the man on the other side of the room, talking with a shorter, redheaded woman, his face lit up with a laugh. Even from far away, he was beautiful. Castiel couldn't help but smile as he walked over, reflecting on the events of the night, how new and wonderful they had been. Dean was unlike anyone he'd ever met. Castiel felt like he had known him all his life, which even he knew was crazy. But the bond that they shared was undeniably strong. Sure, he'd dated other guys before, but this felt so different. So special. Castiel's heart sunk as he realized their relationship wouldn't span any longer than the night.

After a few more steps, he was beside Dean, placing a hand gently on his arm. Dean turned away from his conversation immediately, his eyes lighting up when he saw who it was, and pulled him forward before he could get a word in.

"Charlie, this is Cas." Castiel smiled at the woman in front of him, not missing a beat, and extended his hand. She shook it enthusiastically.

"It's Castiel," he added.

"So this is the famous Cas," she smirked teasingly. He turned to Dean, a puzzled and questioning look on his face, but Dean only rolled his eyes.

"This is the Charlie I was telling you about earlier. The friend who forced me to come tonight."

"_Best _friend," she scolded. Dean smiled at her, nodding his head in agreement, before gazing back down at the man beside him.

"It's very nice to meet you," Castiel replied.

"So, Castiel, you going to stick around a while longer?" she asked, her eyes flicking mischievously between the two men.

"Actually, no," he answered, catching Dean's eye. "That's what I was coming to tell you. I need to, um, get back to my hotel." Dean's smile faltered for only a second before returning, as bright as before.

"I'll walk you out."

"I hope that we will meet again," Charlie interjected dramatically. Castiel smiled, laughing at her inflection. Dean was right; he did like her.

"As do I," he answered, matching her tone before turning towards the exit. As the two made their way through the crowd, Dean placed a hand on Castiel's lower back, guiding him and keeping him close. The touch sent a fresh wave of tingling up his spine and a new feeling of dizziness to his mind. If Dean continued to have this kind of effect on him, he knew that he'd miss his flight.

Once past the crowds and through the cafeteria doors, Dean removed his hand, breaking the connection, and Castiel attempted to clear his head. He still needed to find a way to confess the inevitable ending of the night. Dean's voice pulled him from his thoughts.

"So, d'you have a good time?" He smiled tenderly up at him as they stepped out of the building into the warm evening air, pushing aside her nerves for the moment.

"Yes, I did. Did you?"

"Yeah, big time." Dean smirked teasingly in his direction. Castiel smiled to himself, matching the man's slow pace across the sidewalk.

The area in front of the building was abandoned, letting the two of them have the beautiful night to themselves. There was a light breeze still blowing, cooling the humid air, the temperature not too hot or too cold. A dark, star-filled sky stretched out past the parking lot, the flat horizon making it seem endless. With each step further from the building, light faded behind them, casting a dim glow around the duo's shadows on the ground. Dean breathed in deeply, a calm settling over him as he stepped down off the curb. Perfect nights like made him love his home town, and having Castiel next to him made it so much better.

Castiel cleared his throat lightly, getting Dean's attention as he stopped walking. His stomach was in knots as the man spun to face him. The last thing he wanted to do was tell Dean that he was leaving, and the way he was focusing on him, eyes filled with pure happiness, made his heart ache.

"Thank you for tonight," he said softly, delaying his confession. Dean's warm smile stretched into a lopsided grin.

"For what?"

"Listening, mostly. Caring."

"It's hard not to care about you, Cas." The anxiety in him settled for a moment, feeling at ease under Dean's affectionate gaze.

"Dean, I…" _I have to leave. I can't do this. I'm sorry. _Dozens of explanations flashed through his mind, each as necessary as the next. But, instead of finishing his sentence, Castiel did something he knew he would regret.

Reaching up, he laced his fingers around Dean's neck, pulling him closer until their lips pressed together, foreheads bumping. Dean's arms wrapped around his waist, his grip firm but still gentle, and Castiel let himself fall into the kiss. It was pure, simple, so natural it felt like they had been together for years. They both knew it was absurd, since they barely knew each other, but it felt right. It felt like it was where they belonged. Castiel rested his hand lightly on Dean's shoulder, using him as an anchor when the light-headed feeling settled over him once again. Without warning, Dean pulled back, his forehead still resting against Castiel's.

"Come home with me." The words were out of his mouth before he even knew what he was saying. Sure, he'd been thinking about it all night, but he had never actually considered asking. It was insane, he knew that. He and Castiel were acquaintances, at best. Well, that was before the events in the janitor's closet. Now, their relationship seemed to be up in the air, and Dean realized he wouldn't be at all disappointed if the guy accepted his offer. But Castiel only froze in his arms, eyes wide.

"W-what?"

"Come home with me?" he repeated, unsure, his voice rising at the end. Castiel stepped back, out of his arms, and Dean's hopefulness crumbled. Without saying anything, the man had given him his answer.

Castiel's mind reeled, his emotions clashing as he scrambled for an answer. He yearned to accept the offer, no matter what the consequences, but the sensible part of him stayed grounded. He had a life, a job, and he couldn't throw that away.

"Do you remember how I said that I've been traveling for the past few months?" Confusion etched its way across Dean's face.

"What does that-"

"Just answer the question," he snapped, more annoyed with himself than with the man in front of him. "Do you remember?" Dean nodded warily.

"Well, Kansas is one of my stops." Castiel paused, watching for the realization to sink it, but Dean's expression didn't change. "I'm still going places. Still traveling. Staying here was only temporary." Finally, Dean's face fell, bewilderment replaced by a shroud of disappointment. Silence stretched between them as the excitement in the atmosphere morphed into something much heavier and ominous.

"When do you leave?" he asked dryly, breaking through the dead air.

"My flight takes off at six," Castiel mumbled in reply, averting his eyes to the skyline in the distance. He'd thought telling Dean would make him feel better, but he was wrong. It just made him feel like shit.

"Where you headin'?"

"Washington." Dean's brow furrowed and his jaw clenched as he searched for something to say.

"Well, uh, have a good trip," he added, voice monotone and formal. Castiel's eyes flicked back to his. Even though Dean's voice was emotionless, his half-lit face held all that needed to be said.

"I am sorry, Dean. I really do-"

"Don't worry about it," Dean interrupted, not wanting the conversation to have a bittersweet end. Frankly, he didn't want it to end at all. But, to him, the lesser of two evils was to leave it where it was, not trying to cram any more emotion in the last seconds.

"I guess this is it then?"

"Yeah, I guess so," Dean replied, trying to keep disappointment from creeping into his voice. Castiel peered up at him, crystal blue eyes shining under the outdoor lights. All Dean wanted to do was pull him into his arms and beg him to stay. He knew the thoughts made no sense whatsoever, but they were definitely there. And they weren't going anywhere anytime soon. Swallowing hard, Dean crossed his arms, gaze shifting for just a moment. Castiel took the fidgeting as his cue to leave.

"Goodbye, Dean," he said, gravelly voice swollen with sorrow.

"See ya, Cas," Dean replied, his voice softening. Castiel gave only a hint of a smile before turning and walking to his car, which was parked a few spots away. The door of the Honda civic slammed dully in the silence of the night as he climbed in, the headlights illuminating seconds later. Dean watched from the edge of the black top as Castiel pulled out of the parking space, maneuvering the car out of the lot and onto the open road. His eyes followed the lights as they dimmed in the distance, finally disappearing when the car turned a corner. And, just like that, Castiel was gone.

"God dammit…" Dean let his arms fall, eyes clenching shut. How could he have been so stupid? Putting himself out there and hoping for the best. Until tonight, he thought he knew better. Apparently not. Dean cursed himself as tears pricked the corners of his eyes. He should _not _be getting this worked up over one guy. A guy he barely even knew. It was idiotic, senseless, completely unlike him, and yet, he couldn't help the grief that had welled up inside. His thoughts were cut short when the doors to the school opened, a small group of drunk and cackling adults tumbling out. The noise snapped him out of his state.

Dean shook off what he could of his emotion and made his way across the sidewalk, duking inside behind the group. Blanking his mind, he stepped back into the cafeteria, hoping the noise and buzz of the party would block out whatever stupid emotions were swirling around within him. But before he could get even a few feet past the entrance, Charlie appeared beside him, almost like she'd been waiting.

"You're still here?" she asked, concern laced through her voice. Turning slowly, Dean faced her, not wanting to have the conversation that went along with her inquiry.

"Where else would I be?" He only hoped his tone would deter her from continuing.

"Oh, I just thought you would, ya know," she shrugged, averting her eyes, "leave with Castiel."

_So much for forgetting about him. _Rather than arguing that he wouldn't do that, which was obviously a lie, he skipped right to the explanation.

"Nah. He, uh, he has a flight to catch in the morning."

"You _do_ know how Rom-Com that sounds, right?" she remarked, smirking.

"Yeah, Charlie, I do," he huffed in reply. At the moment, his friend wasn't helping. At all.

"Don't worry, Dean. There are plenty of-"

"I swear to God, if you say there are other fish in the sea…"

"Fine, fine, sorry." Charlie held her hands up in mock surrender. But his glare made her arms fall to her sides. He was truly torn up about what had happened.

"You really like him, don't you?" Dean only shrugged, casting his gaze down the floor. "Don't you lie to me, Dean Winchester!"

"Fine! Yes! I do! But it doesn't really matter anymore." Charlie sighed loudly, sympathy for her heartbroken friend coursing through her.

"He likes you, too. A lot." At this, Dean glanced up again, meeting her eyes.

"How d'ya know?"

"It was super obvious. I mean, the way he looked at you? That's how princess looks at her prince after he's saved her from a fire-breathing dragon." Laughing lightly at her analogy, Dean felt his spirits being lifted.

"Ya think?"

"No, I _know_." His smile grew as he pulled Charlie into his arms, hugging her tight.

"What would I do without you?"

"Die, probably," she replied, sighing dramatically into his chest. He chuckled as she pulled away.

"I'm gonna go, but I'll give you a call this week, 'kay?"

"You better," she warned. "Sam is putting the task of getting you out of your apartment more on _my_ shoulders, and I'd appreciate some help." Dean rolled his eyes.

"You two gotta stop plotting behind my back." Charlie smirked, her eyes glinting mischievously. "And, thanks, by the way. For making me get off my ass and come here tonight."

"I knew you wouldn't regret it." Returning his best friend's grin, Dean gave her shoulder one last squeeze.

"Later, Charlie."

* * *

**A/N: If you've come to the end of this chapter, thank you so much for reading! It turned out to be very long, but I promise the remaining ones will be much shorter. Anyways, review are much appreciated if you'd like to tell me what you think of this chapter and the story so far! Thanks!**


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